U.S. Pat. Nos. 3,678,098 and 3,702,799 discuss the state of the art of reacting epihalohydrins with a number of different organic compounds to provide a great variety of products. These patents relate more particularly to the production of unsaturated acid ester monomers, including acrylic or methacrylic acid esters, to produce useful quaternary ammonium salt monomers capable of reacting with monomers containing vinyl unsaturation by addition polymerization.
Filed on even date herewith and having the same assignee is an application entitled "Halohydroxypropyl Quaternary Ammonium Monomers and Polymers Derived Therefrom" directed to monoethylenically unsaturated quaternary ammonium salt monomers which are readily polymerizable with vinyl acetate and to the polymers produced therefrom. Also filed on even data herewith and assigned to the assignee of the instant application is an application entitled "Halohydroxypropyl Dialkyl-ar-vinylphenylenylalkyenyl Quaternary Ammonium Compounds, Polymers Thereof, And Uses Of Such Polymers As Wet Strength Agents" directed to monoethylenically unsaturated quaternary ammonium salt monomers containing aromatic components and to the polymers of such monomers.
The above identified patents and applications relate to monomers which comprise a halohydroxypropyl quaternary ammonium group, in common with the instant application. While the above-identified patents and applications provide useful compounds, the monomers are generally water-soluble salts which are insoluble in many organic solvents and potential comonomers. These monomers have strong base cations, in general, and in their polymers and copolymers this strongly cationic behavior persists. In contrast, monomers of the instant application are generally organic soluble, have a less pervasive ionic character and this lesser degree of ionic character persists in the polymers of these monomers. Homo- and copolymers of such monomers, methods and articles are also disclosed. Thus, the polymers of the instant monomers may be compounded with anionic materials, such as pigments and thickeners, without encountering severe coagulation or stability problems. These goals are achieved while maintaining, in the polymer, the desired low energy cure characteristics, i.e. curability, preferably at ambient or somewhat higher temperatures such as 20.degree. C. to 100.degree. C.